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Lycopodium Alkaloids: Isolation and Asymmetric Synthesis

  • Mariko Kitajima
  • Hiromitsu Takayama
Chapter
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 309)

Abstract

Lycopodium alkaloids have attracted the attention of many natural product chemists and synthetic organic chemists due to their important biological activities and unique skeletal characteristics. In this review we describe isolation and asymmetric syntheses of several new alkaloids such as lycoposerramines-C, -V, -W, and cernuine, and show that asymmetric total synthesis played a key role in elucidating the structures of these complex natural products.

Graphical Abstract

Keywords

Alkaloid Asymmetric synthesis Isolation Lycopodium Structure elucidation 

Abbreviations

AChE

Acetylcholine esterase

CBS

Corey–Bakshi–Shibata

CDI

Carbonyl diimidazole

DIAD

Diisopropyl azodicarboxylate

DMP

Dess–Martin periodinane

DPPA

Diphenylphosphinyl azide

dppf

1,1′-Bis(diphenylphosphino)ferrocene

DTAD

Di-tert-butyl azodicarboxylate

IBX

2-Iodoxybenzoic acid

Ipc

Isopinocampheyl

NMO

N-Methylmorpholine oxide

Ns

Nosyl

TASF

Tris(dimethylamino)sulfonium difluorotrimethylsilicate

Teoc

2-(Trimethylsilyl)ethoxycarbonyl

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Copyright information

© Springer-Verlag Berlin Heidelberg 2011

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesChiba UniversityChibaJapan

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